Windsor Holidays

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Your Windsor Holiday

Take the hassle out of planning your next exciting adventure with a Windsor holiday package. Whether you've come for its art, food, architecture or something else, this city offers limitless opportunities for discovery. Fill your trip to Windsor with tours of some of its top attractions. First up? Make a move for Wolf Creek State Park. Browse Expedia's extensive range of travel options and book your dream holiday to Windsor today.

Windsor Holiday

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Decatur Airport (DEC)
Population
1,150
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Shelbyville Beach, Wolf Creek State Park and Eagle Creek State Park

Our pick of the best Windsor Hotel Deals

Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 1 Sept to 2 Sept
AU$147
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (794 reviews)
"Very nice stay"

Reviewed on 19 Aug. 2025

Comfort Suites Mattoon East
Holiday Inn Express & Suites Mattoon by IHG

Holiday Inn Express & Suites Mattoon by IHG

2.5 out of 5
121 Swords Dr, Mattoon, IL
Fully refundable
The price is AU$169 per night from 7 Sept to 8 Sept
AU$169
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (732 reviews)
"Convenient and friendly. Good complimentary breakfast."

Reviewed on 2 Aug. 2025

Holiday Inn Express & Suites Mattoon by IHG
Hilton Garden Inn Mattoon, Il

Hilton Garden Inn Mattoon, Il

3 out of 5
100 Coles Centre Parkway, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 29 Aug to 30 Aug
AU$233
29 Aug - 30 Aug
includes taxes & fees
8.8/10 Excellent! (178 reviews)
"convenient"

Reviewed on 10 Aug. 2025

Hilton Garden Inn Mattoon, Il
See all 68 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices on Expedia for your Windsor getaway. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and better availability in January, February and November. Explore our cheap Windsor holiday packages and you could get some great off-season discounts.
How many days is enough for Windsor?
With a well-planned schedule, you can easily visit the main Windsor sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Windsor holiday for longer.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Windsor package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging stays and flights individually. Better still, you can personalise your Windsor trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Windsor?
If you've got your Windsor holiday dates locked in, book as soon as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Windsor?

  1. Pick your dates: The things you'd like to do in Windsor and your preferred season will help you decide when to go.
  2. Set a budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Windsor. Then, select a property that matches your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the ideal Windsor holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.